The present invention relates to the compound defined according to the structure: ##STR4## as well as compounds defined according to the genus: ##STR5## wherein Z represents one of the moieties: ##STR6## use of the compound having the structure: ##STR7## as an intermediate for producing the compound having the structure: ##STR8## and uses of the foregoing compounds in augmenting or enhancing the aroma or taste of consumable materials such as foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfumed compositions, perfumed articles, smoking tobacco compositions or smoking tobacco articles. Also the present invention relates to a process for producing the compound having the structure: ##STR9## by rearranging the compound having the structure: ##STR10##
There has been considerable work performed relating to substances which can be used to impart (augment or enhance) flavors and fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials some of which may be in short supply and to provide more uniform properties in the finished product.
Vanilla-like, sweet, fruity, raspberry anisic, ionone-like, and jammy aroma and taste characteristics are highly desirable for many uses in foodstuff, chewing gum, toothpaste, medicinal product and chewing tobacco flavors.
Vanilla-like, raspberry-like and ionone-like aroma nuances are highly desirable in several types of perfume compositions, colognes and perfumed articles, e.g., perfumed polymers and anionic, cationic, nonionic and zwitterionic solid or liquid detergents.
Sweet, vanilla-like, heliotropin-like, fruity, juicy, rum, and sugary nuances are highly desirable in smoking tobacco prior to smoking and sweet, smoothing rich, vanilla-like, creamy, rum-like, fruity and caramellic aroma and taste nuances are high desirable in smoking tobacco on smoking in the main stream and in the side stream.
Specifically, a need has arisen for the use of powerful and long lasting vanilla type aroma and taste compounds and raspberry-like compounds in consumable materials in view of the need to use much smaller quantities than when using the heretofore known vanilla-like and raspberry-like aroma and/or taste imparting and/or augmenting compounds.
Fenaroli's Handbook of Flavor Ingredients, Second Edition, Vol. 2, Published by the CRC Press of Cleveland, Ohio discloses at page 196 the use in flavor of ethyl vanillin having the structure: ##STR11## indicating that it has "an intense vanilla odor and sweet taste". It further is indicated that the flavoring power of this compound is 2-4 times stronger than vanillin. Fenaroli's Handbook of Flavor Ingredients also indicates at page 561 that veratraldehyde having the structure: ##STR12## has a use in food flavors and has a very sweet, woody, vanilla-like odor and a warm, sweet and vanilla-like taste. Fenaroli's Handbook of Flavor Ingredients also indicates at page 560 that vanillin itself having the structure: ##STR13## has a strong vanilla-like odor and a very sweet taste and is useful in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums and the like.
Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)" published in 1969, at monograph 1363, also indicates the use in food flavors and fragrances of ethyl vanillin having the structure: ##STR14## and Arctander further indicates "ethyl vanillin is often used to substitute a larger amount of vanillin in the fragrance when a discoloration problem arises due to the active hydroxyl or aldehyde groups of the vanillin/ethyl vanillin molecules". Arctander also discloses at monograph 1364, isoethyl vanillin having the structure: ##STR15## and indicates that it has a "sweet, somewhat floral odor remotely reminiscent of vanilla but much weaker than ethyl vanillin and also weaker than vanillin". Arctander further indicates at monograph 1365, that 3-methoxy-4-ethoxy benzaldehyde otherwise known as "Homo veratraldehyde" having the structure: ##STR16## has a sweet, somewhat floral odor remotely reminiscent of vanilla, more so than commercial ethyl vanillin, but not with the same strength and has a sweet, vanilla-like taste of approximately two times the power effect of vanillin. At monograph 3067, Arctander indicates the use of vanillin itself in foodstuffs and fragrances. At monograph 3068, Arctander indicates the use in flavors and fragrances of isovanillin having the structure: ##STR17## Arctander indicates that "isovanillin" is practically odorless when cold; mild, floral, herbaceous or Hay-like at room temperature, and very sweet, balsamic-Vanilla-like when heated above 60.degree. C. Arctander also indicates that the material as such is rarely used in perfumes or flavors since its aromatic value is too inconspicuous, but it has some importance since it occurs along with Vanillin in one of the many processes used for the manufacture of vanillin.
European Published Patent Application No. 31253, published on July 1, 1981, entitled "Process for preparing 3,4-substituted benzaldehydes" (assigned to the Sumitomo Chemical Company, Limited of Japan) discloses a genus of compounds defined according to the structure: ##STR18## wherein R.sub.1 and/or R.sub.2 represent hydrogen or alkyl having from one up to four carbon atoms or R.sub.1 or R.sub.2 may jointly form an alkylene group having from one to four carbon atoms. The compound having the structure: ##STR19## is specifically set forth in a list located in claim 18 on page 34 of said published application, and furthermore the compound having the structure: ##STR20## is also specifically set forth at lines 30 and 31 on page 21 of said application. No organoleptic characterization is given for the compound nor is a specific method of preparation for said compound set forth or exemplified in said published European Patent Application No. 31253. Indeed, the compound is not characterized in any way whatsoever except for naming it in a large list of compounds contained within the generic structure: ##STR21##
Beilstein, Volume E II 8, page 283, System No. 773, discloses 4-Methoxy-3-athoxy-benzaldehyde having the structure: ##STR22## and indicates that it is a crystal having a melting point of 50.degree.-51.degree. C. and can be prepared by reaction of isovanillin and ethyl iodide.
Beilstein, Volume E III 8, at page 2024, also indicates that the compound having the structure: ##STR23## can be prepared by reacting 3-hydroxy-4-methoxy-benzaldehyde with diethyl sulfate in the presence of sodium hydroxide or methanolic KOH.
Chem. Abstracts, Vol. 25, at pages 3325 and 3326 (1931) indicates that the compound having the structure: ##STR24## has a pronounced vanillin odor. This abstract is of Ber. 64B, 274-80 (1931).
Nothing in the prior art however discloses any compound defined according to the structure: ##STR25## wherein Z is represented by one of the moieties: ##STR26## or organoleptic uses thereof.